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101 Stadium Drive, Chesapeake
$649,900
4 Beds ⋅ 3.1 Baths ⋅ 10655286 MLS
Welcome to your very own homesteader’s haven in the heart of Chesapeake! Tucked away on over an acre, this one-of-a-kind brick ranch offers a blend of modern comfort and timeless, back-to-the-land charm. Outside, you'll be greeted by a flourishing orchard with established fruit trees that provide a bounty through every season, blueberries, figs and plums for jam-making, crisp apples, cherries, peaches, pomegranates, and pecans for baking. Designed for self-sufficiency with two outbuildings, a 40’x45’ parking area ideal for your boat or RV, solar panels and a new roof provide energy savings. The fully finished converted garage for an in-law suite, playroom, fifth bedroom, business front, the choice is yours. If you’re dreaming of tending gardens and evenings under the trees enjoying the fruits of your own land, this property has it all. A true little piece of paradise, right in the city yet worlds away. This home also has an assumable VA mortgage at 4.9% interest for a VA eligible buyer! Perfect opportunity for owning a home in Chesapeake that meets all of your space needs, enjoying self sufficiency and all the convenience that Chesepeake has to offer.

101 Stadium Drive, Chesapeake

609 Dupree Lane, Chesapeake
$350,000
3 Beds ⋅ 2.1 Baths ⋅ 10654902 MLS
Welcome to 609 Dupree Lane, a spacious 3-story end-unit townhome offering 3 bedrooms, 2.5 baths, and a thoughtfully designed layout. The first floor features a versatile flex room, ideal for a home office, den, fitness space, or additional living area. The main living level showcases new flooring, recessed lighting, and a generously sized kitchen featuring a large center island, pantry, and plenty of space for gathering and entertaining. Step outside to the second-floor balcony for additional outdoor living space. The spacious primary suite offers a walk-in closet and private bath with double bowl sinks. Additional highlights include new ceiling fans and an attached 2-car garage. Enjoy low-maintenance living with grounds upkeep included, along with community amenities featuring a clubhouse, pool, and playgrounds. A wonderful combination of space, style, and convenience in Chesapeake!

609 Dupree Lane, Chesapeake

2156 Edwin Drive, Chesapeake
$577,740
3 Beds ⋅ 3 Baths ⋅ 10655240 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more -all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Estimated Completion December 2026. Photos are to be used as an example and do not represent exact listings selections.

2156 Edwin Drive, Chesapeake

2180 Edwin Drive, Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10655238 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2180 Edwin Drive, Chesapeake

2184 Edwin Drive, Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10655236 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2184 Edwin Drive, Chesapeake

2182 Edwin Drive, Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10655235 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2182 Edwin Drive, Chesapeake

911 Bainbridge Boulevard, Chesapeake
$529,000
4 Beds ⋅ 3 Baths ⋅ 10655168 MLS
NEW CONSTRUCTION Welcome home to this beautifully designed 4-bedroom, 3-bath residence offering modern style and exceptional comfort. The open-concept floor plan features 9-foot ceilings, a spacious family room with a cozy gas fireplace, and a stunning kitchen with granite countertops, stainless steel appliances, and abundant cabinet space. A first-floor bedroom with a full bath is ideal for guests or multi-generational living. The luxurious primary suite offers an oversized tiled shower, double vanity, and a large walk-in closet. Generous secondary bedrooms, ample storage, pull-down attic access to a full attic, Energy Star double-pane windows, and extensive insulation provide year-round efficiency and comfort. Completing this exceptional home is a detached 2-car garage with electricity and plenty of additional storage. Also has a rear alley entrance and a huge fenced backyard. Ready in less than 45 Days.

911 Bainbridge Boulevard, Chesapeake

708 Pebble Quay, Chesapeake
$705,000
4 Beds ⋅ 3 Baths ⋅ 10655182 MLS
Unique custom built home on cul-de-sac with rare 3 car attached garage and extended driveway. This house was made for entertaining - 23' x 14' screened porch off family room for extended living space, along with a 22' x 20' pavilion - both with trek decking, finished wood ceilings, recessed lights and fans. Beautiful extensive landscaping with a stamped concrete walkway winding around house. Impressive 2 story entry has gorgeous chandelier. Dual staircases. Large kitchen includes granite counters, stainless steel appliances with gas stove, tons of cabinets and counterspace as well as deep pantry and eat-in nook. Formal living room and dining room with door leading to large front porch. First floor office in addition to 4 bedrooms upstairs. Full bathroom downstairs. Hardwood floors run through entire 1st floor. Primary bedroom includes corner gas fireplace, 13'x12.5' walk-in closet, and large bathroom with dual sinks and jetted tub . Laundry room has entire wall of cabinets with counter space and fold down ironing board. Lots of built in storage throughout, including a walk in climate controlled attic closet. The rare 3 car garage (owner actually has 4 cars in there!) is decked out for a car aficionado with LED lighting covering the ceiling and rubberized flooring. Additional outside shed. 16 hardwired cameras around exterior convey. Generator hook up in garage. Top of the line outside Charbroil kitchen conveys with acceptable full price offer. Neighborhood dock with boat ramp nearby. Very active River Walk Community Association centers around the beautiful clubhouse (which can be rented) and has a tennis/pickleball court w/pickleball league, garden club, swimming pool w/swim team, concerts in fall, food trucks and more, as well as parks and playgrounds. Tree lined walking paths wind through neighborhood along lakes with gazebos and fountains. Easy to hop on nearby Rt. 168 Chesapeake Expressway to easily get to any area of Hampton Roads.

708 Pebble Quay, Chesapeake

2609 Mossgate Court, Chesapeake
$399,900
4 Beds ⋅ 2.1 Baths ⋅ 10652642 MLS
Opportunity knocks in Chesapeake! This property offers a chance to create something truly special in a desirable location. Bring your vision and your renovation plans to unlock the full potential of this home. The expansive lot is a standout feature, providing an abundance of space and endless possibilities for outdoor living, entertaining, gardening, recreation, or future improvements. Whether you're an investor searching for your next project or a buyer looking to build equity and make a home your own, this property is ready for its next chapter. Conveniently located near shopping, dining, schools, parks, major roadways, and everything Chesapeake has to offer. Properties with this much potential and land don't come around every day. Come see the possibilities for yourself! Schedule your showing today!

2609 Mossgate Court, Chesapeake

2107 Stalham Road, Chesapeake
$369,900
5 Beds ⋅ 2.1 Baths ⋅ 10654947 MLS
Hard-to-find first-floor bedroom! This well-maintained 5-bedroom, 2.5-bath Chesapeake home delivers the space, flexibility and convenience buyers are looking for. The spacious downstairs bedroom is ideal for guests, a home office, workout room or versatile flex space, while four additional bedrooms upstairs provide plenty of room to spread out. The kitchen features granite countertops and stainless-steel appliances and opens to the den, creating an easy flow for everyday living and entertaining. Step outside to the backyard for even more room to enjoy. Built in 2000 with a comfortable two-story layout and generous living areas, this home is ready for its next owner. Conveniently located near shopping, restaurants, military bases and major commuting routes with easy access throughout Hampton Roads. Five bedrooms, flexible living space and a great Chesapeake location—this one checks a lot of boxes!

2107 Stalham Road, Chesapeake

4332 Hillingdon Bend Unit 206, Chesapeake
$227,000
2 Beds ⋅ 2 Baths ⋅ 10653350 MLS
Welcome home! This beautiful residence features an open floor plan and soaring nine-foot ceilings. The layout includes two bedrooms and two full bathrooms, highlighted by a primary suite with dual closets. The kitchen is equipped with stainless steel appliances and ample cabinetry, flowing seamlessly into the main living and dining areas. Additional interior features include central air conditioning, forced air heating, and dedicated washer and dryer hookups. As part of a common-interest community, this property offers one assigned parking space and access to shared amenities, including a swimming pool, grounds maintenance, and trash removal. Conveniently located near major highways, military bases, local shipyards, and the retail options surrounding Chesapeake Square, this home is perfectly positioned. Call today to schedule your private showing!

4332 Hillingdon Bend Unit 206, Chesapeake

1004 Cedar Tree Court, Chesapeake
$679,580
4 Beds ⋅ 3 Baths ⋅ 10655160 MLS
Welcome to the Whitehurst model in Cedar Manor! Currently under construction with an estimated Spring 2027 completion, this stunning 2-story transitional floor plan offers 3,054 square feet of thoughtfully designed living space on a generous 0.68-acre corner lot with serene pond views. Featuring 4 or 5 spacious bedrooms, 3 full baths, and a desirable main-floor layout, this home boasts a primary bedroom suite on the first level complete with a spacious ensuite and walk-in closet. The light-filled interior includes a foyer, natural gas fireplace, open breakfast area, dedicated office/study or 5th bedroom, utility room with main-floor laundry, and a walk-in attic for abundant storage. Energy efficient features included a tankless gas water heater and radiant barrier. Enjoy cul-de-sac living conveniently near to top-rated Grassfield schools. Take advantage of seller incentives available when using the trusted lender. Contact us for full details, floor plans, and construction updates! Pictures from prior build. We have this floor plan to walk in another community!

1004 Cedar Tree Court, Chesapeake

1511 Hazel Avenue, Chesapeake
$335,000
3 Beds ⋅ 1.1 Baths ⋅ 10654700 MLS
This charming 3-bedroom, 1.5-bath ranch offers comfortable one-level living with a fresh, updated feel. Upgrades include: New electrical panel (2026), paint (2026), carpet (2026), flooring (2026) and moisture barrier (2026). Creating a clean, inviting interior that is move-in ready and waiting for someone to make it their own. The functional floor plan provides plenty of space for everyday living and entertaining as well as a bonus area that can be used as a second living room, play area or office space. Enjoy the spacious backyard, ideal for relaxing or gathering with friends, plus a shed offering additional storage or workshop space. Located in an established neighborhood convenient to shopping, dining, bases and major roadways. Schedule your private showing today!

1511 Hazel Avenue, Chesapeake

1016 Thoroughgood Way Unit 302, Chesapeake
$225,000
2 Beds ⋅ 2 Baths ⋅ 10654835 MLS
Welcome to Village at Gateway in the heart of South Norfolk! This beautifully maintained third-floor condo is easily accessed via elevator and features an open-concept floor plan with oversized rooms and abundant natural light from skylights. The upgraded kitchen provides ample cabinetry, a pantry, and bar seating for four for casual dining or entertaining. Enjoy indoor-outdoor living with a spacious 8x12 covered porch just off the living room. The primary suite includes a glass-enclosed shower and dual closets, while the second bedroom is generously sized for guests or a home office. Additional highlights include in-unit stacked washer and dryer, secured building access, and gated parking with fob entry. Conveniently located near shopping, dining, and major interstates, don’t miss this opportunity for low-maintenance living!

1016 Thoroughgood Way Unit 302, Chesapeake

1540 Eldwick Drive #202, Chesapeake
$300,130
2 Beds ⋅ 2 Baths ⋅ 10655131 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, listed price reflects $10K incentive taken off price of home, see agent for details. Our Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #202, Chesapeake

2217 Nantucket Avenue, Chesapeake
$649,900
4 Beds ⋅ 2.1 Baths ⋅ 10655107 MLS
The beautiful 4 bdrm Camellia model has a projected delivery date of Nov 2026. Throughout this charming, tree-lined neighborhood are an assortment of exceptional amenities, including a resort-style pool, community trails, pocket parks & plazas w/ outdoor seating, a playground, natural preservation areas, & state-of-the-art clubhouse w/ kitchen, conference room, & fitness center. This homes kitchen features upgraded granite countertops, subway tile backsplash, & an appliance package complete w/ gas range! Crown molding & durable luxury vinyl plank throughout 1st level. Gas fireplace w/ granite surround & walk-in attic featuring ample storage space. Primary bdrm w/ lighted tray ceiling & WIC, features an en-suite that includes a double vanity, soaking tub, & 5' shower. Enjoy water views from the spacious backyard! Gas heat & tankless hot water heater. CALL FOR FINANCING SPECIALS!

2217 Nantucket Avenue, Chesapeake

1644 Chesapeake Drive, Chesapeake
$365,000
4 Beds ⋅ 2.1 Baths ⋅ 10655000 MLS
Beautiful 4 Bedroom Home with Modern Updates and Spacious Layout This stunning 4-bedroom, 2.5-bath home features fresh paint, new carpet, and stainless-steel appliances throughout. The open floor plan creates a seamless flow that’s perfect for entertaining and cooking, with large, bright rooms that feel warm and welcoming.Enjoy a formal dining room, a comfortable family room, and a charming breakfast nook. A cozy fireplace adds the perfect touch for relaxing evenings.Step outside and take your entertainment outdoors to your private, fenced-in backyard — ideal for gatherings, play, or quiet mornings.At the end of the day, retreat to the primary suite, complete with a spacious ensuite bathroom, offering comfort and privacy. LOCATED CLOSE TO BASES, MEDICAL, INTERSTATES, ENTERTAINMENT, BEACHES AND RETAIL.

1644 Chesapeake Drive, Chesapeake

901 Stewart Street, Chesapeake
$215,000
2 Beds ⋅ 1 Baths ⋅ 10655021 MLS
Welcome to 901 Stewart Street! This charming 2-bedroom, 1-bath ranch offers comfortable single-level living in the South Norfolk area of Chesapeake. With approximately 825 square feet, the home features a functional layout with plenty of opportunity to make the space your own. Enjoy a spacious yard with room for outdoor entertaining, gardening, or creating your own outdoor retreat. Conveniently located near shopping, dining, major roadways, and everyday amenities, this property offers easy access throughout Chesapeake and surrounding Hampton Roads. Whether you're looking for your next home or an investment opportunity, 901 Stewart Street is ready for its next chapter. Schedule your private showing today!

901 Stewart Street, Chesapeake

3208 Pineridge Drive, Chesapeake
$525,000
5 Beds ⋅ 3.1 Baths ⋅ 10654949 MLS
Classic character meets seriously usable space. Tucked beneath the trees in the highly desirable Silverwood neighborhood, this 5 bedroom, 3.5 bath Dutch Colonial brings together original character and thoughtful updates without losing its charm. Natural light fills the rooms and plays across the original refinished hardwood floors, bringing warmth throughout the 2,602 square foot home. The brand-new kitchen brings new cabinetry, countertops, appliances and LVP, while the stunningly updated bathrooms add a fresh, polished finish. A gas fireplace adds another touch of original character to the living room, and the finished room over the garage offers flexible space for whatever the home needs. The EZBreeze porch takes outdoor living a step further, with heat and air conditioning that keep the space comfortable throughout all the seasons. Whether enjoying a mild morning or settling in on a cooler evening, this is outdoor space with the comfort to make it genuinely usable year-round. A home with the kind of character you notice right away, paired with a fresh kitchen, beautiful updates, and spaces that make you want to stay awhile. Move in with nothing to do!

3208 Pineridge Drive, Chesapeake

1514 Myrtle Avenue, Chesapeake
$339,900
3 Beds ⋅ 2 Baths ⋅ 10654924 MLS
The possibilities are endless with this spacious ranch-style home! Offering a flexible layout ideal for multi-generational living, the home features two separate living areas and bathrooms with a shared kitchen and laundry. A separate side entrance leads to the rear living space with a large bedroom, walk-in shower and private living area, offering great potential for an in-law suite or extended family. The large kitchen offers a pantry and tons of cabinet space, with neutral colors and updated windows throughout. Major improvements include a new roof, newer HVAC, 2026 furnace, encapsulated crawl space with dehumidifier and new sewer line from the home to the street. Enjoy a fenced backyard, storage shed and fantastic detached garage with plenty of room for vehicles, workshop, hobbies or storage. Convenient to shopping and everyday amenities. Seller will be holding an estate sale; some listing photos have been AI-enhanced to digitally remove personal belongings and estate sale items to better showcase the rooms and space.

1514 Myrtle Avenue, Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.